Manufacture of extreme pressure additives for lubricating oils



Patented Apr. 17, 1951 MANUFAUIURE OF EXTREME PRESSURE ADDITIVES FORLUBRICATING OILS Kenneth Charles Roberts, Clayton, Manchester, England,assignor to The Anchor Chemical Company Limited, Clayton, Manchester,England, a British company No Drawing. Application February 12, 1948,Se-

rial No. 8,002. In Great Britain December 23,

Section 1, Public Law 69 0, August 8, 1946 Patent expires December 23,1966 2 Claims.

This invention relates to the manufacture of new materials forincorporation in mineral lubricating oils with a view to improving theirperformance under conditions of extreme pressure.

2 these features lead to improved extreme pressure properties when thesulphurised esters are incorporated in lubricating oils.

The manner in which the invention is carried The use of sulphurisednaturally-occurring 5 out will now be described by reference to someanimal, vegetable and fish oils as extreme presspecific examples. sureadditives is well known but sufiers from the Emmple 1 limitation thateven under the most favourable conditions m about 0 by Weight of SulphurThe glycol ester of the acids of rape seed 011 can be combined with thenatural oils without (100 parts by Weight) in reaction With sulphurrendering them incompatible with mineral lubri- (20 parts y Weight) anddicycloheXylamme eating oils. Combined sulphur is an operative (2 pa tsby Weight) for 5 hours at 160 C. yielded component of extreme pressureadditives of this a Clear, p ed V scous liquid having a free sultype,and it is the object of the invention to pro- D tent of Only 0.3%, atotal sulphur convide sulphrised esters which contain increased tent of15-16% and complete freedom from proportions of combined sulphur andwhich will phurous Odours- The product w 4 freeiy impart improvedextreme pressure characteristics miscible with Well-known grades of mmera1 t lubricating 1 A 5% blend of this ester with a mineral oil hadAccording to my invention, nomgelatinised $111. the relatively highTimken O. K. value of 60 lbs. phurised products having a relatively highcon- Example 3 tent of combined sulphur are prepared b reacting sulphurwith unsaturated esters of mono- 016,54 ester of Seed aclds (150 anddihydric aliphatic alcohols with the naturally tammg d 1cyc1heXy1amme (3was treated. at occurring fatty acids containing 16 to 24 carbon WlthSulphur 3 5' When E reactuin atoms, in the presence of adicyclohexylamine. 25 mlxture P been mamfiained at 160 for 6/2 For thepurpose of my invention either the alcohours Wlth ,constant stlrrmg theproduct was holic or the acidic component of the ester or both red O11free Sulphur content of 02% may be unsaturated Thus, unsaturated monoand a viscosity at 200% F. of 336 Redwood No. 1 and dihydric aliphaticalcohols may be combined s with either saturated or unsaturated fattyacids 50 Example 3 V of the type specified or saturated aliphatic alco-The allyl ester of rape seed acids 150 g.) was hols of the typespecified may be combined with treated with dicyclohexylamine andsulphur as unsaturated fatty acids. The proportion of sulin Example 2.The resulting viscous red oil had phur used may be appreciably greaterthan that a free sulphur content of 0.11% and a viscosity used in thesulphurisation of the corresponding at 200 F. of 704 Redwood No. 1seconds.

glycerides. Example 4 The sulphurised products obtained by this processpossess those desirable physical and chem- Sperm oil, which for thepurpose of my inical characteristics of a sulphurised oil additivevention may be considered to consist essentially which are found in thecorresponding sulphurised of unsaturated esters resulting from thecomglycerides prepared by the method claimed in bination of highermonohydric aliphatic almy copending application Serial No. 645,972, nowcohols with higher fatty acids. (400 g.) Was Patent No. 2,450,384,including low corrosiveness treated for '7 hours at 180 C. with sulphur(50 2;.) due to their low content of free sulphur and relaanddicyclohexylamine (10 g.) The product, tively low viscosity. Inaddition, the new sulwhich was a soft red wax at ordinarytemperaphurised products possess the further desirable tures, had a freesulphur content of 0.25% and characteristics of improved compatibilitywith a viscosity at 200 F. of 120 Redwood No. 1 secmineral lubricatingoils and a higher content of onds. The Timken O. K. value of a standardcombined sulphur than is obtainable in liquid mineral oil was raisedfrom 18 to 30 on incorporaproducts made by sulphurising glycerides. Bothtion of 5% of this product.

3 Example 5 The triethylene glycol ester of soya fatty acids (150 g.)was treated with dicyclohexylamine and sulphur as in Examples 2 and 3.The resulting red oil had a free sulphur content of 2.14% and aviscosity at 200 F. of 252 Redwood No. 1 seconds.

Example 6 In similar manner to that used in the preceding examples, theethyl ester of soya fatty acids was sulphurised to yield a relativelymobile red oil having a free sulphur content of 1.45% and a viscosity at200 F. of 54 Redwood No. 1 seconds.

What I claim is:

1. In the production of extreme pressure additives for lubricating oils,the process which consists substantially in heating and reacting sulfurwith an unsaturated ester of an aliphatic alcohol containing not morethan two hydroxyl groups and naturally occurring fatty acids containingfrom 16 to 24 carbon atoms, in the presence of a small amount of adicyclohexylamine, at a temperature within the range of from about 130to 180 C., and recovering the resulting sulfurized product.

2'. The process of claim 1 wherein sperm oil is used as the unsaturatedester component of the reaction.

KENNETH CHARLES ROBERTS.

REFERENCES CITED The following references are of record in the file ofthis patent:

UNITED STATES PATENTS Number Name Date 1,669,491 Savage May 15, 19282,152,185 Gottesmann Mar. 28, 1939 2,427,717 Dearborn Sept. 23, 1947

1. IN THE PRODUCTION OF EXTREME PRESSURE ADDITIVES FOR LUBRICATING OILS,THE PROCESS WHICH CONSISTS SUBSTANTIALLY IN HEATING AND REACTING SULFURWITH AN UNSATURATED ESTER OF AN ALIPHATIC ALCOHOL CONTAINING NOT MORETHAN TWO HYDROXYL GROUPS AND NATURALLY OCCURRING FATTY ACIDS CONTAININGFROM 16 TO 24 CARBON ATOMS,IN THE PRESENCE OF A SMALL AMOUNT OF ADICYCLOHEXYLAMINE, AT A TEMPERTURE WITHIN THE RANGE OF FROM ABOUT 130*TO 180* C. AND RECOVERING THE RESULTING SULFURIZED PRODUCT.